Toluene → 2,4-Di-tert-butyl-6-[piperidin-1-yl-(4-trifluoromethyl-phenyl)-methyl]-phenol

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Reaction Steps

8.29 g (97.33 mmol) of piperidine are added, at room temperature, to a solution of 7.74 g (44.43 mmol) of trifluoromethylbenzaldehyde in 50 ml of toluene. The slightly yellow-colored solution is boiled under reflux for 4 hours; approximately 1 ml of water is separated off using a water separator, and a solution of 8.73 g (42.32 mmol) of 2,4-di-tert-butylphenol in 15 ml of toluene is then added dropwise. The reaction mixture is boiled at reflux for further 17 hours and then cooled to room temperature; the solvent is distilled off using a vacuum rotary evaporator. Crystallisation of the residue from iso-propanol/methanol (1:1) yields 15.04 g (79%) of compound (201) (Table 2), m.p. 150-152° C. Molecular weight C27H36F3NO (447.59). Analysis, calculated: C 72.45; H 8.11; N 3.13%. Analysis, found: C 72.63; H 8.05; N 3.05%. 1HNMR (300 MHz, CDCl3, ppm): 1.12 (s, 9H); 1.39 (s, 9H); 1.56 (m, 4H); 2.28 (bm, 6H); 4.37 (s, 1H); 6.65 (d, 1H); 7.08 (d, 1H); 7.47 (m, 4H).

Provenance & Evidence